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Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones
[Image: see text] Taking aryl propargyl ether and o-iodibenzoic acid as substrates, a series of aryl cyclolactones bearing an exocyclized C=C bond were constructed with moderate to good yields. Diverse substituent groups could be tolerant in the reaction, which indicated excellent compatibility of t...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8793066/ https://www.ncbi.nlm.nih.gov/pubmed/35097300 http://dx.doi.org/10.1021/acsomega.1c06177 |
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author | He, Hua-Feng Wang, Yuwan Zou, Chun Tu, Zheng Xu, Yongquan Yin, Junfeng |
author_facet | He, Hua-Feng Wang, Yuwan Zou, Chun Tu, Zheng Xu, Yongquan Yin, Junfeng |
author_sort | He, Hua-Feng |
collection | PubMed |
description | [Image: see text] Taking aryl propargyl ether and o-iodibenzoic acid as substrates, a series of aryl cyclolactones bearing an exocyclized C=C bond were constructed with moderate to good yields. Diverse substituent groups could be tolerant in the reaction, which indicated excellent compatibility of the reaction. In this tandem reaction, Ag(2)O was employed as the media and Et(3)N was screened as the base to facilitate the reaction. A concise mechanism was proposed on the basis of the expansion of the substrates and theoretical analysis. Sonogashira type coupling coupled with intramolecular nucleophilic addition in one pot to construct the product, 3-ethylideneisobenzofuran-1(3H)-one. |
format | Online Article Text |
id | pubmed-8793066 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-87930662022-01-28 Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones He, Hua-Feng Wang, Yuwan Zou, Chun Tu, Zheng Xu, Yongquan Yin, Junfeng ACS Omega [Image: see text] Taking aryl propargyl ether and o-iodibenzoic acid as substrates, a series of aryl cyclolactones bearing an exocyclized C=C bond were constructed with moderate to good yields. Diverse substituent groups could be tolerant in the reaction, which indicated excellent compatibility of the reaction. In this tandem reaction, Ag(2)O was employed as the media and Et(3)N was screened as the base to facilitate the reaction. A concise mechanism was proposed on the basis of the expansion of the substrates and theoretical analysis. Sonogashira type coupling coupled with intramolecular nucleophilic addition in one pot to construct the product, 3-ethylideneisobenzofuran-1(3H)-one. American Chemical Society 2022-01-11 /pmc/articles/PMC8793066/ /pubmed/35097300 http://dx.doi.org/10.1021/acsomega.1c06177 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | He, Hua-Feng Wang, Yuwan Zou, Chun Tu, Zheng Xu, Yongquan Yin, Junfeng Ag(2)O-mediated Tandem Reaction between Terminal Alkyne and o-Iodibenzoic Acid: Construction of 3-Ethylideneisobenzofuran-1(3H)-ones |
title | Ag(2)O-mediated Tandem Reaction between
Terminal Alkyne and o-Iodibenzoic Acid: Construction
of 3-Ethylideneisobenzofuran-1(3H)-ones |
title_full | Ag(2)O-mediated Tandem Reaction between
Terminal Alkyne and o-Iodibenzoic Acid: Construction
of 3-Ethylideneisobenzofuran-1(3H)-ones |
title_fullStr | Ag(2)O-mediated Tandem Reaction between
Terminal Alkyne and o-Iodibenzoic Acid: Construction
of 3-Ethylideneisobenzofuran-1(3H)-ones |
title_full_unstemmed | Ag(2)O-mediated Tandem Reaction between
Terminal Alkyne and o-Iodibenzoic Acid: Construction
of 3-Ethylideneisobenzofuran-1(3H)-ones |
title_short | Ag(2)O-mediated Tandem Reaction between
Terminal Alkyne and o-Iodibenzoic Acid: Construction
of 3-Ethylideneisobenzofuran-1(3H)-ones |
title_sort | ag(2)o-mediated tandem reaction between
terminal alkyne and o-iodibenzoic acid: construction
of 3-ethylideneisobenzofuran-1(3h)-ones |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8793066/ https://www.ncbi.nlm.nih.gov/pubmed/35097300 http://dx.doi.org/10.1021/acsomega.1c06177 |
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